Executive Assistant/Chief of Staff (CEO Support)

Cyvl•Boston, MA

3d•$20 - $40

About The Position

This is a high-trust, high-impact role supporting a venture-backed startup CEO. You’ll help keep both the company and the CEO running at full speed by eliminating friction, staying ahead of problems, and turning chaos into a clean plan. The split is roughly 60–70% work support / 30–40% personal support, depending on week-to-week needs. If you love building systems, making plans, and being the person who “just gets it done,” you’ll do well here. What You’ll Own Work: ~60–70% CEO operations + communication Proactively manage the CEO’s calendar: scheduling, prioritizing, confirming, and protecting focus time Draft and polish emails (investors, customers, partners) in the CEO’s voice Coordinate meetings end-to-end: scheduling, agenda prompts, notes capture, and follow-ups Execution + organization Maintain task lists and a lightweight “CEO operating system” (weekly priorities, follow-ups, reminders) Track action items from meetings and ensure nothing drops Update and maintain CRM (e.g., HubSpot): notes, next steps, pipeline hygiene after customer calls Travel + logistics Book flights/hotels/ground transport; build clean itineraries Handle changes fast (delays, reschedules, cancellations—because travel loves drama) Coordinate event logistics and meeting clusters while traveling Personal: ~30–40% Manage life admin: appointments (doctor, dentist, etc.), renewals, recurring tasks Thoughtful reminders and execution: birthdays, gifts, important dates Household logistics: research vendors, get quotes, schedule services (example: sofa reupholstery—source options, call shops, compare, book, and coordinate pickup/drop-off) Set up recurring grocery orders and other “autopilot” routines What Success Looks Like (First 30–60 Days) Calendar runs smoothly with fewer last-minute scrambles Inbox is calmer because drafts and follow-ups are handled quickly and cleanly HubSpot stays accurate without the CEO needing to think about it Travel is booked efficiently with clear itineraries and backups Personal errands/admin happen without prompting (the dream)

Requirements

Based in the Boston area with availability for occasional in-person errands/hand-offs
10–20 hours/week with responsiveness during agreed windows
Experience with (or ability to quickly learn): Google Calendar/Gmail, spreadsheets, task tools, and CRM basics (HubSpot a plus)
Reliable computer, phone, and internet
Highly ambitious grad student or early-career operator
Extremely organized and allergic to things falling through the cracks
Proactive: you don’t wait to be asked; you notice, flag, and fix
Fast, accurate, and discreet (you’ll handle sensitive info)
Strong written communicator with good judgment and tone
Comfortable on the phone coordinating vendors and services
Boston-area local who can do occasional in-person tasks reliably

Nice To Haves

Prior EA, chief of staff, ops, consulting, or startup experience
Comfortable building simple systems (templates, checklists, workflows)
Interest in startups/venture and learning how CEOs actually operate

Responsibilities

Proactively manage the CEO’s calendar: scheduling, prioritizing, confirming, and protecting focus time
Draft and polish emails (investors, customers, partners) in the CEO’s voice
Coordinate meetings end-to-end: scheduling, agenda prompts, notes capture, and follow-ups
Maintain task lists and a lightweight “CEO operating system” (weekly priorities, follow-ups, reminders)
Track action items from meetings and ensure nothing drops
Update and maintain CRM (e.g., HubSpot): notes, next steps, pipeline hygiene after customer calls
Book flights/hotels/ground transport; build clean itineraries
Handle changes fast (delays, reschedules, cancellations—because travel loves drama)
Coordinate event logistics and meeting clusters while traveling
Manage life admin: appointments (doctor, dentist, etc.), renewals, recurring tasks
Thoughtful reminders and execution: birthdays, gifts, important dates
Household logistics: research vendors, get quotes, schedule services (example: sofa reupholstery—source options, call shops, compare, book, and coordinate pickup/drop-off)
Set up recurring grocery orders and other “autopilot” routines